Ashley’s ex tells HollywoodLife.com exclusively that it doesn’t surprise him she fell for Bentley or Brad!

BacheloretteAshley Hebert started her search for love on The Bachelor where she fell hard for notorious player Brad Womack, the two-time Bachelor who left his first season single, breaking the hearts of DeAnna Pappas and Jenni Croft. Ashley then continued her journey as The Bachelorette only to be lead on by jerk Bentley Williams. But this isn’t the first time. Her ex-boyfriend — who asked to remain anonymous for privacy reasons — tells HollywoodLife.com exclusively that Ashley has a past of chasing the wrong guys and that her insecurities caused her problems in relationships before she ever met Brad or Bentley!

“I couldn’t believe some of the things Bentley was saying, but it doesn’t surprise me [that Ashley fell for him],” her ex admits, since there was a bad boy that got between them!

Ashley began dating her ex when she started dental school at The University of Pennsylvania, meeting through their dental fraternity. But the relationship had problems because there were other guys that got in the way. “There were always other people involved,” remembers her ex. “There were other people that were jealous. I don’t know if she still had feelings for those people — she told me she didn’t. It was way more complicated than I realized.”

“The other guy that was always kind of the instigator of any issues that we had is more of [a] bad boy” Ashley’s ex explains. “It was frustrating because I felt like we had something, [but] it was always something preventing us.”

Ashley‘s insecurities added to the failure of her graduate school relationship. “She always thought that she was going to get hurt,” says the ex. And after a short summer separation, Ashley’s issues became more apparent. “When we got back together that fall — again back to the insecurities — I remember her specifically saying that, ‘I don’t think you should date me.'”

And like she does now, Ashley hides her self-doubt behind a smile. “Her personality, her bubbliness, is almost more of nervousness,” explains her ex.

But Ashley has always known that she’s looking for Mr. Right — and that’s why her ex feels that she went on the show. “She was always about finding someone to fall to fall in love with,” he shares. “Her true personality is portrayed on there — it’s the same stuff, different guy — always feeling some kind of insecurity or not really knowing how to be about something.”

He knows that despite her uncertainties, that Ashley is a total catch. “She’s smart. She’s beautiful,” he gushes. “The initial thing that drew me to her was her personality. It was [just] always an issue of timing and people being involved and the time with those situations.”

“I wish her the best in finding love,” says Ashley’s ex. “I know that’s what she’s focused on and hoping for.”